CN109457469A - A kind of method of Friedel-Crafts alkylation to aramid fiber surface modification - Google Patents
A kind of method of Friedel-Crafts alkylation to aramid fiber surface modification Download PDFInfo
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- CN109457469A CN109457469A CN201811190295.8A CN201811190295A CN109457469A CN 109457469 A CN109457469 A CN 109457469A CN 201811190295 A CN201811190295 A CN 201811190295A CN 109457469 A CN109457469 A CN 109457469A
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- Prior art keywords
- aramid fiber
- friedel
- fiber surface
- surface modification
- crafts alkylation
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- 229920006231 aramid fiber Polymers 0.000 title claims abstract description 45
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims abstract description 15
- 230000004048 modification Effects 0.000 title claims abstract description 14
- 238000012986 modification Methods 0.000 title claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 239000000835 fiber Substances 0.000 claims abstract description 15
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims abstract description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000005530 etching Methods 0.000 claims description 7
- 238000004090 dissolution Methods 0.000 claims description 5
- 239000012153 distilled water Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- 238000004140 cleaning Methods 0.000 claims description 2
- 230000002000 scavenging effect Effects 0.000 claims description 2
- 238000004506 ultrasonic cleaning Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 5
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 230000003670 easy-to-clean Effects 0.000 abstract description 2
- 239000002131 composite material Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 125000003963 dichloro group Chemical group Cl* 0.000 description 2
- 239000003733 fiber-reinforced composite Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 1
- 239000011157 advanced composite material Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000003486 chemical etching Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/11—Compounds containing epoxy groups or precursors thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/07—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof
- D06M11/11—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof with halogen acids or salts thereof
- D06M11/17—Halides of elements of Groups 3 or 13 of the Periodic Table
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/08—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with halogenated hydrocarbons
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/16—Synthetic fibres, other than mineral fibres
- D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M2101/34—Polyamides
- D06M2101/36—Aromatic polyamides
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention discloses a kind of Friedel-Crafts alkylations to the method for aramid fiber surface modification, important is by a series of step application Friedel-Crafts alkylation on aramid fiber surface phenyl ring grafted epoxy chloropropane and its by-product.According to a large amount of phenyl ring are contained on aramid fiber strand, herein according to its molecular structure feature, using classical organic chemical reactions-Friedel-Crafts alkylation, grafted epoxy chloropropane and its by-product on aramid fiber surface phenyl ring.Friedel-Crafts reaction mild condition reacts and is easy to carry out, and treatment process is simple, and fiber is easy to clean after reaction, provides the new thinking and direction for being easier to large-scale industry implementation for aramid fiber surface modification.
Description
Technical field
The present invention relates to polymeric material fields, more particularly, to a kind of Friedel-Crafts alkylation to aramid fiber surface
Modified method.
Background technique
Aramid fiber reinforced composite has been widely used for aerospace, military affairs, machinery as a kind of advanced composite material
Equal fields, extreme enrichment and improve people's lives, have broad application prospects.
Aramid fiber is a kind of novel high score with the excellent properties such as high intensity, high-modulus, high temperature resistant, resistant to chemical etching
Sub- material.But in aramid fiber composite material preparation process, amide group is difficult to react with the atom of resin or group, table
Face shows biggish chemical inertness, and the interface bonding energy of aramid fiber and resin is lower, and adhesiveness and wellability are poor, and two-phase interface is viscous
Tie undesirable, and load is all that stress transfer is carried out by interface, causes the interlaminar shear strength of composite material low, shadow
The performance for having rung composite material combination property limits its application in the composite.It can be seen that by aramid fiber
Surface carries out necessary processing to improve fiber and basal body interface compatibility, the mechanical property for improving aramid fiber enhancing composite material
There can be important practical significance.
Currently, domestic and foreign scholars have done some work in terms of the modification of aramid fiber surface, physical modification is mainly concentrated
In chemical modification, some new method of modifying have also been developed in recent years, the application is exactly one of them.
Summary of the invention
In order to improve the interface performance of aramid fiber reinforced composite, the purpose of the present invention is to provide a kind of friedel-craft alkyl
Change reaction to the method for aramid fiber surface modification.
In order to realize above-mentioned purpose of the present invention, the technical scheme adopted by the invention is that a kind of Friedel-Crafts alkylation pair
The method of aramid fiber surface modification, includes the following steps:
(1) suitable halogenated alkyl reagent is dissolved in dichloromethane solution, obtains solution I；
(2) fiber is put into the container equipped with acetone, is cleaned by ultrasonic, then washes with water, dries, to thoroughly remove virtue
Synthetic fibre fiber surface coating；
(3) tow after step (2) drying is put into reaction vessel, anhydrous aluminum chloride, methylene chloride is added, carries out ultrasound
Dissolution mixing, while pre-etching is carried out to fiber surface；
(4) solution I is slowly added dropwise in the reaction vessel of step (3), after reacting a period of time, with acetone, is steamed
Distilled water cleaning obtains the modified aramid fiber in surface.
In a preferred embodiment of the invention, which is characterized in that in step (1), the halogenated alkyl reagent is
Epoxychloropropane or other reagents with halogenated alkyl, content are the 5~30% of solution.
In a preferred embodiment of the invention, which is characterized in that in step (2), the temperature of the ultrasonic cleaning is
60~80 DEG C, scavenging period is no less than 2hr.
In a preferred embodiment of the invention, which is characterized in that in step (3), the addition methylene chloride
Amount is 50~100 times of fiber quality, and anhydrous aluminum chloride is 5~10 times of fiber quality, and the reaction time of the pre-etching is
0.5~1hr maintains the temperature at 40~50 DEG C.
In a preferred embodiment of the invention, which is characterized in that in step (4), the time of the reaction is 0.5
~4hr.
Beneficial effects of the present invention are as follows:
The characteristics of according to a large amount of benzene ring structures are contained on aramid fiber strand, utilize classical organic chemical reactions-Fu-
Gram alkylated reaction grafted epoxy chloropropane and its by-product on aramid fiber surface phenyl ring.Friedel-Crafts reaction mild condition, instead
It should be easy to carry out, treatment process is simple, and fiber is easy to clean after reaction, provides one for aramid fiber surface modification and is easier to
The new thinking and direction that large-scale industry is implemented.
Detailed description of the invention
Fig. 1 (a) is untreated original aramid fiber SEM figure in the present invention.
Fig. 1 (b) is that aramid fiber is schemed through the SEM of Friedel-Crafts alkylation 1hr in the embodiment of the present invention 1.
Fig. 1 (c) is that aramid fiber is schemed through the SEM of Friedel-Crafts alkylation 2hr in the embodiment of the present invention 2.
Fig. 1 (d) is that aramid fiber is schemed through the SEM of Friedel-Crafts alkylation 4hr in the embodiment of the present invention 3.
Fig. 2 is the tensile strength variation diagram that Aramid Fibre/Epoxy Composites are activated front and back.
Specific embodiment
The present invention is further illustrated by the following examples, but these embodiments must not be used to explain to the present invention
Limitation.
Embodiment 1
(1) 10.0g epoxychloropropane reagent is dissolved in 90.0g dichloromethane solution, obtains solution I；
(2) 1.0g aramid fiber is put into the container equipped with 100mL acetone, is cleaned by ultrasonic 3hr in 60 DEG C of sinks, so
After wash with water, dry, to thoroughly remove aramid fiber surface coating；
(3) tow after step (2) drying is put into reaction vessel, 5.0g anhydrous aluminum chloride and 100.0g dichloromethane is added
Alkane carries out ultrasonic dissolution mixing in 40 DEG C of thermostatic water baths, while carrying out pre-etching, reaction time 30min to fiber surface；
(4) solution I is slowly added dropwise in the reaction vessel of step (3), reacts 1hr, is cleaned, obtained with acetone, distilled water
The aramid fiber modified to surface.
Embodiment 2
(1) 15.0g epoxychloropropane reagent is dissolved in 90.0g dichloromethane solution, obtains solution I；
(2) 2.0g aramid fiber is put into the container equipped with 100mL acetone, is cleaned by ultrasonic 4hr in 70 DEG C of sinks, so
After wash with water, dry, to thoroughly remove aramid fiber surface coating；
(3) tow after step (2) drying is put into reaction vessel, 10.0g anhydrous aluminum chloride and 200.0g dichloro is added
Methane carries out ultrasonic dissolution mixing in 50 DEG C of thermostatic water baths, while carrying out pre-etching to fiber surface, and the reaction time is
60min；
(4) solution I is slowly added dropwise in the reaction vessel of step (3), reacts 2hr, is cleaned, obtained with acetone, distilled water
The aramid fiber modified to surface.
Embodiment 3
(1) 20.0g epoxychloropropane reagent is dissolved in 150.0g dichloromethane solution, obtains solution I；
(2) 2.0g aramid fiber is put into the container equipped with 100mL acetone, is cleaned by ultrasonic 5hr in 80 DEG C of sinks, so
After wash with water, dry, to thoroughly remove aramid fiber surface coating；
(3) tow after step (2) drying is put into reaction vessel, 10.0g anhydrous aluminum chloride and 200.0g dichloro is added
Methane carries out ultrasonic dissolution mixing in 50 DEG C of thermostatic water baths, while carrying out pre-etching to fiber surface, and the reaction time is
60min；
(4) solution I is slowly added dropwise in the reaction vessel of step (3), reacts 4hr, is cleaned, obtained with acetone, distilled water
The aramid fiber modified to surface.
After the tensile strength of the modified aramid fiber in obtained surface after embodiment 1-3 processing is tested with it is unmodified
Preceding aramid fiber tensile strength test compares, referring to fig. 2, it is known that, the surface obtained after handling in embodiment 1-3 changes
Property the tensile strength of aramid fiber be obviously improved, wherein the tensile strength of embodiment 3 is promoted the most obvious.
Claims (5)
1. a kind of Friedel-Crafts alkylation is to the method for aramid fiber surface modification, which comprises the steps of:
(1) suitable halogenated alkyl reagent is dissolved in dichloromethane solution, obtains solution I；
(2) aramid fiber is put into the container equipped with acetone, is cleaned by ultrasonic, then washes with water, dries, to thoroughly remove fibre
Dimension table finishing coat；
(3) tow after step (2) drying is put into reaction vessel, anhydrous aluminum chloride, methylene chloride is added, carries out ultrasonic dissolution
Mixing, while pre-etching is carried out to fiber surface；
(4) solution I is slowly added dropwise in the reaction vessel of step (3), after reacting a period of time, with acetone, distilled water
Cleaning obtains the modified aramid fiber in surface.
2. a kind of Friedel-Crafts alkylation as described in claim 1 exists to the method for aramid fiber surface modification, feature
In in step (1), the halogenated alkyl reagent is epoxychloropropane or other reagents with halogenated alkyl, content are
The 5~30% of solution.
3. a kind of Friedel-Crafts alkylation as described in claim 1 exists to the method for aramid fiber surface modification, feature
In in step (2), the temperature of the ultrasonic cleaning is 60~80 DEG C, and scavenging period is no less than 2hr.
4. a kind of Friedel-Crafts alkylation as described in claim 1 exists to the method for aramid fiber surface modification, feature
In in step (3), the amount of the addition methylene chloride is 50~100 times of fiber quality, and anhydrous aluminum chloride is fiber quality
5~10 times, reaction time of the pre-etching is 0.5~1hr, maintains the temperature at 40~50 DEG C.
5. a kind of Friedel-Crafts alkylation as described in claim 1 exists to the method for aramid fiber surface modification, feature
In in step (4), the time of the reaction is 0.5~4hr.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201811190295.8A CN109457469A (en) | 2018-10-12 | 2018-10-12 | A kind of method of Friedel-Crafts alkylation to aramid fiber surface modification |
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| CN201811190295.8A CN109457469A (en) | 2018-10-12 | 2018-10-12 | A kind of method of Friedel-Crafts alkylation to aramid fiber surface modification |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109882543A (en) * | 2019-03-20 | 2019-06-14 | 台州格雷科胶带有限公司 | Noise-reduction energy-saving type ethylene propylene diene rubber V-ribbed belt |
| CN109971096A (en) * | 2019-04-09 | 2019-07-05 | 鲁东大学 | A kind of preparation method of high tenacity PVC composite material film |
| CN112250940A (en) * | 2020-10-27 | 2021-01-22 | 长春工业大学 | Lewis acid-loaded chopped carbon fiber reinforced polyolefin composite material and preparation method thereof |
| CN114243217A (en) * | 2022-02-24 | 2022-03-25 | 湖南中锂新材料科技有限公司 | Lithium ion battery composite diaphragm and preparation method thereof |
| CN115873238A (en) * | 2023-02-23 | 2023-03-31 | 烟台泰和新材高分子新材料研究院有限公司 | Meta-aramid polymer with grid structure and preparation method and application thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109882543A (en) * | 2019-03-20 | 2019-06-14 | 台州格雷科胶带有限公司 | Noise-reduction energy-saving type ethylene propylene diene rubber V-ribbed belt |
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| CN109971096A (en) * | 2019-04-09 | 2019-07-05 | 鲁东大学 | A kind of preparation method of high tenacity PVC composite material film |
| CN109971096B (en) * | 2019-04-09 | 2022-01-28 | 鲁东大学 | Preparation method of high-toughness PVC composite material film |
| CN112250940A (en) * | 2020-10-27 | 2021-01-22 | 长春工业大学 | Lewis acid-loaded chopped carbon fiber reinforced polyolefin composite material and preparation method thereof |
| CN114243217A (en) * | 2022-02-24 | 2022-03-25 | 湖南中锂新材料科技有限公司 | Lithium ion battery composite diaphragm and preparation method thereof |
| CN114243217B (en) * | 2022-02-24 | 2022-05-13 | 湖南中锂新材料科技有限公司 | Lithium ion battery composite diaphragm and preparation method thereof |
| CN115873238A (en) * | 2023-02-23 | 2023-03-31 | 烟台泰和新材高分子新材料研究院有限公司 | Meta-aramid polymer with grid structure and preparation method and application thereof |
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Application publication date: 20190312 |
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